


Win/Win

by Inell



Series: Tumblr 600 Followers Celebration [16]
Category: Teen Wolf (TV)
Genre: Alternate Universe - College/University, Alternate Universe - Fraternity, Anal Fingering, And He Helps His Frat Bros Out, Bets & Wagers, Bottom Vernon Boyd, Hand Jobs, M/M, Reference to Isaac Lahey/Stiles Stilinski, Reference to Jackson Whittemore/Stiles Stilinski, Rimming, Sex Toys, Stiles is Sexually Open
Language: English
Status: Completed
Published: 2016-03-29
Updated: 2016-03-29
Packaged: 2018-05-29 23:13:27
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,610
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6397924
Author URL: https://archiveofourown.org/users/Inell/pseuds/Inell
Summary: <blockquote class="userstuff">
              <p>Stiles should have known not to bet Boyd over a stupid football game. Fortunately, it's a win/win for both of them.</p>
            </blockquote>





	Win/Win

**Author's Note:**

  * For [crazydorkyhomo](https://archiveofourown.org/gifts?recipient=crazydorkyhomo).



> For my 600 Follower Celebration, crazydorkyhomo prompted: Stoyd,rimming, college, some type of bet was made and the loser has to rim the winner, rating is whatever you make it
> 
> I had so much writing this. Hope you enjoy!

“You’re serious, aren’t you?” Stiles stares at Boyd, fully aware he’s gaping but unable to help himself because he’s not sure he heard what he thinks he heard. “That’s really what you want for winning the bet?”

“No, I’m Boyd,” Boyd says dryly. He smirks slightly when Stiles blinks at him. “And, yes, that’s what I want.”

“Wow. Okay.” Stiles shakes his head, huffing laugh. “You’ve managed to throw me for a loop, big guy. I honestly wasn’t expecting this. I was prepared to have to wash your car wearing a skimpy speedo or maybe get stuck with bathroom clean-up duty for a month.”

“Are you complaining?” Boyd arches a brow. “I can always change my mind.” He looks solemn for a moment. “Obviously, if you aren’t interested, I’ll think of something else. I’m not going to force you.”

“Dude, that’s totally not an issue. _At all_.” Stiles looks Boyd over in a blatantly appreciative way. “I just wasn’t aware that you swung my way. If I’d realized you do, I’d have been trying to climb you like a tree months ago. Damn! All that wasted time. We could have been doing this since we moved into the frat house, you know?”

“You’re an idiot,” Boyd deadpans. Stiles doesn’t take offense because Boyd totally doesn’t mean it. Much. “So, do we have a deal or not?”

“Duh.” Stiles snorts. “I’ve got a hot guy wanting my tongue in his ass. What do you think?”

“I think I want to hear you consent to it before we proceed,” Boyd tells him firmly.

“Boyd, I’d eat your ass with or without the bet,” Stiles says matter-of-factly. “You know I’m always willing to help a brother out, anyway. All you’ve got to do is ask.”

There are definitely perks to being a bisexual frat boy, that’s for sure. Even dealing with the straight guys who just want hand jobs so they can still claim they’re straight are fun, especially when Stiles is so good they come back for more. Fortunately, most of his frat brothers are pretty sexually open, so there’s usually someone else horny and single whenever he gets an urge. Boyd’s one of the few frat brothers he _hasn’t_ had in one way or another, so he’s pretty excited about having the opportunity now.

“I’ve heard,” Boyd says, lips curving slightly. “Why do you think I’ve finally given in to trying you out? Isaac hasn’t shut about your mouth for weeks, and I swear Jackson’s about ready to propose to your dick.”

“Jackson’s a total size queen, and I love it,” Stiles admits, waggling his eyebrows. “And Isaac’s welcome to brag about me all he wants if it brings me new partners.” He licks his lips. “So, I need to ask, have you ever done anything with a guy before or is this your first time?”

“It’s not my first time.” Boyd watches him curiously. “I’ve never been rimmed, however, which is why I thought it would make a good prize for winning the bet.”

“The bet you totally cheated at, by the way, but whatever. I think we’re both winners here,” Stiles points out. “Do you want me to touch your dick? Can I use my fingers or do you just want my tongue? How do you want it? I mean, teasing and playful or a little rough? Anything else you want? Boyd, you okay there? You’re looking a little overwhelmed.”

Boyd frowns. “I didn’t realize there would be so many questions.” He runs his hand over his face. “You can do whatever you want, alright? Tongue or fingers, touch my dick or don’t touch, and I’d prefer teasing to rough. I’m not really into rough unless I’m in a certain mood, which isn’t often.”

Thinking about Boyd being in the mood for rough _does things_ to Stiles. He usually prefers topping, but he’s versatile, and the thought of Boyd pinning him to the bed and just taking really gets his dick leaking. He clears his throat, noticing the slightly amused smile on Boyd’s lips. “Smirk while you can, big guy,” he warns as he stands up. “Pretty soon, you’ll be begging me to come.”

“We’ll see,” Boyd taunts. “I’m not sure you’re nearly as good as our brothers’ claim. Figure it’s time I find out, though, after having to listen to all the talk and seeing you prancing around for months.”

“I don’t prance,” Stiles scoffs. “And I’m _better_ than they claim. You’ll find out soon enough, then you’ll know what the fuss is all about.” He smiles. “Just don’t fall in love with me. I’m too young to settle down just yet.”

“I think you have enough boys half-assed in love with you,” Boyd tells him. “I’ll try to guard my heart, though.”

“Such a sassy mouth on you,” Stiles teases, opening the drawer of his dresser with all his sex toys. He gets the bottle of lube and a medium sized dildo out, grabbing one of his thick plugs, too, before shutting the drawer. “Do you want me to lock the door?”

Boyd considers the question for a moment, obviously thinking about how often their frat brothers just come into rooms unannounced with no concept of privacy because he finally nods. “Yes, I’d rather not have an audience. I’m not really into that.”

“Some people aren’t, and that’s totally cool.” Stiles locks the door before walking over to his bed. He tosses his toys and the lube on the bed before facing Boyd. “You sure you’re okay with this? I can totally wash your car if you’ve changed your mind.”

“I’m more than okay with this, Stiles. I’ve been looking forward to it since you foolishly bet on a football game,” Boyd tells him. “I think you wanted to lose, which makes me believe you thought I’d request something sexual anyway.”

“Well, I might have had a few fantasies about it, but I figured it was just wishful thinking,” Stiles admits. “I honestly thought you were straight until tonight.”

“Definitely not.” Boyd grins. “Now, how do you want me?”

“Loaded question.” Stiles snickers as he pulls his shirt over his head. “Get naked and then kneel on the bed. Do you have to go wash up?”

“I took care of that before I came to your room,” Boyd says, ducking his head slightly as if he’s shy talking about cleaning his ass. “It should be good.”

“I’m glad you actually thought ahead and took care of it.” Stiles is being totally honest because some guys don’t think or even care if they’re clean before trying to get Stiles to rim them. While he’s very sexually open and hasn’t met too many kinks he’s not willing to try at least once, that happens to be one area where he’s a little particular.

“So get naked and kneel, huh?” Boyd pulls his shirt over his head before unfastening his jeans. Once he’s shoved them down and taken his socks off, he’s standing in his underwear, and Stiles takes a moment to enjoy the view. Boyd’s tall and well-built, his shoulders, arms, and thighs worthy of worship, without a doubt. When he slides down his underwear, his dick bounces into view.

It’s long with an average thickness, already half-hard, seeming to harden even more as Stiles stares. He wants that pretty dick in his mouth, he decides, so he’s going to rim Boyd so fucking well that he’ll get addicted to having Stiles’ tongue in his ass and come back for more. Then Stiles can get that dick in his mouth. Something to look forward to. Stiles pushes his sweatpants down as Boyd crawls onto the bed.

“That’s one fine ass, Boyd,” Stiles murmurs, picking up the lube and plug from where he put it earlier. “I’m going to use this plug on myself. Do you want to watch me finger my ass so I can take it?”

“No. I want to loosen you up and fuck you with it,” Boyd tells him bluntly, dark eyes practically smoldering as he stares at Stiles.

“Fuck, that’s a better option, for sure.” Stiles crawls onto the bed and wiggles around until he’s on his knees in front of Boyd. He holds onto the wall as Boyd drizzles cold lube between his cheeks, biting his lip to keep from lecturing Boyd about warming up lube first because, really, it’s a minor discomfort, and he’s about to have those large fingers in his ass. It’s a fair trade-off. Boyd drags his fingers over his hole, teasing him, making him push his ass back for more. Finally, he pushes a finger inside, his lips brushing against Stiles’ lower back as he begins to fuck him.

“You’re so tight,” Boyd says. “Can’t believe you’re so fucking tight. Want to fuck you sometime. Feel that hole clenching around me.”

“I’m totally onboard with that idea.” Stiles groans when a second finger pushes inside him. “God, your fingers are so thick.”

“Not as thick as your dick.” Boyd reaches around him to tug on his dick. “Can see why Jackson’s obsessed with it. Could make those college boy porn films if you ever need money with that monster.”

“Dude, it’s not that huge,” Stiles mutters, feeling warmth splotch on his face. He knows he’s got a big dick, but it’s not a monster by any means. “Stop trying to fluster me.”

“Why? You’re cute when you’re blushing.” Boyd adds a third finger, fucking him until he’s rolling his hips back for more. When Stiles’ is about to ready to forget the bet and just fuck himself on Boyd’s fingers, Boyd pulls his hand away. Then the plug is being pushed inside, snug and perfect. Boyd slaps his ass cheek just hard enough to sting. “All set. My turn now.”

“Right. Definitely your turn.” Stiles gets off the bed and walks around to the foot of it. When he crawls onto it, he makes himself comfortable and spreads Boyd’s ass cheeks. He blows on Boyd’s hole, soft puffs of air, then he leans in to drag the flat of his tongue from balls on up. He licks that way for a bit, feeling Boyd’s ass flex beneath his hands. Boyd is quiet, not making many noises at all, and it’s almost a challenge to Stiles to make him lose control enough to not be quiet.

With that in mind, Stiles begins licking Boyd’s hole. He laps at it, tracing the pucker with his tongue, even spitting once just to see if that type of thing turns Boyd on. It doesn’t seem to, which is actually a relief because Stiles’ isn’t really into the whole porn spitting thing some guys seem insistent on doing. When some of his frat brothers’ only experience with another man is watching gay porn, it can lead to some interesting, and sometimes entertaining, reality checks for them. Isaac and Jackson are both also bi, though, so they have experience, and that might be why they’re two of Stiles’ favorites. Well, that and the fact they also take him on dates, which is nice. Maybe Boyd will be into dating, too.

When Stiles presses his tongue inside Boyd’s hole, he hears a low gasp. That makes him start moving his tongue more, wanting another noise from Boyd. The plug in his ass feels good, filling him up, but he can’t help but think how awesome it would be if one of their brothers were here, too, fucking him as he eats Boyd’s ass. Maybe another time. For now, he focuses on fucking Boyd with his tongue, releasing his cheeks as he can reach around Boyd and jerk his dick. He’s a little thicker now that he’s fully hard, pre-come leaking from the head of his dick that Stiles uses as lube as he strokes his dick.

After tongue fucking Boyd for a while, Stiles goes back to licking and teasing, moving his mouth lower and sucking on Boyd’s balls. He stops jerking his dick and strokes his hole, feeling it quiver beneath his fingertips. Boyd’s breathing heavily, his back slick with sweat, and there have been a few more noises since that first one. Stiles grabs the lube, squirting some into his palm and warming it up before drizzling it onto Boyd’s hole, rubbing it all over the pucker before pressing a finger into Boyd’s ass.

“You like that?” he asks, spanking one of Boyd’s firm ass cheeks and feeling him react to the light swat. Oh yes, he likes that, too. Stiles grins as he swats his ass a few more times, working in a second finger. “You’re so tight, big guy. Bet you haven’t had anyone in this pretty little hole for months. I wanna fuck you, wanna spread you around my dick, wanna make you come so hard.”

“Fuck,” Boyd growls, pushing back against Stiles’ fingers. That’s when Stiles add a third, moving them in and out, stretching them to loosen his hole. “Do it.”

“Maybe next time,” Stiles murmurs. He definitely wants to fuck Boyd, but not tonight. They haven’t talked about going that far, and he’s not going to take the chance that Boyd’s so far gone that he’s consenting just because of the amazing sex. Stiles isn’t one of those douchebag frat boys who takes advantage of people during sex, after all. He’s been on the receiving end of that once back in high school, and he’s vowed to never do that to anyone else no matter what.

Stiles pulls his fingers out of Boyd’s ass and reaches for his dildo. After grabbing a condom off his bedside table and sliding it over the toy, he presses the blunt end against Boyd’s ass. Boyd actually moans when Stiles works the toy into his ass, which makes Stiles lean down to lick at his hole where it’s stretched around the dildo. He starts fucking him with the toy, in and out, feeling him start to roll his hips and press back for more.

“Oh yeah. Take that toy,” he murmurs, shifting it slightly until he hears Boyd’s breath catch. He smirks because he knows he’s got the perfect angle now, is pretty sure the dildo is rubbing against Boyd’s prostate. “You should see how pretty you look, sweaty and desperate while fucking yourself on the toy, probably so turned on that you’ll come without even having your dick touched.”

“Can’t. Need to touch,” Boyd says, fingers gripping Stiles’ blanket tightly. Stiles understands. Not everyone can come untouched, after all. He reaches around Boyd, jerking his dick, twisting his wrist just so while fucking the dildo in and out of Boyd’s ass.

“Come for me,” he urges, biting down lightly on Boyd’s ass cheek. Boyd stiffens, grunting as he suddenly shoots ropes of come onto Stiles’ hand and blanket. Stiles keeps fucking the toy into him, milking his dick until he’s completely spent and soft. Only then does he pull the dildo out, rolling the condom off and tossing it on the bed. He’s so hard it only takes a dozen strokes before he’s coming, dripping down onto Boyd’s hole and lower back.

“Was that really necessary?” Boyd asks, looking over his shoulder and smiling slightly. “Marking your territory?”

“You betcha.” Stiles grins at him. “It’s a fun way to say Stiles was here, don’t you think?” He winks before falling back onto the bed. “Stop your bitching, big guy. It’s time for round two.”

“Round two?” Boyd makes a noise when Stiles begins to licking his come off his ass, his head going back down and his body pressing back against Stiles’ face. “I’m so fucking glad I won that bet.”

**Author's Note:**

> [Tumblr](http://inell.tumblr.com)


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